Drunken Flirting
by soulofawinchester
Summary: She's had a crush on Dean for a while now, but has never let him know. When they get into a drinking contest at a local bar, things end up differently than either of them expected.
1. Chapter 1

Author: soulofawinchester

Character(s): Dean Winchester, Sam Winchester, Grace

Type: One Shot

POV: First Person, Grace

Word Count: 1561

Warnings: Drinking

Note: I kind of used the imagine title as a base for where this one shot went, but I hope you like it anyway. :)

The rum burned my throat as it went down. But I was determined to beat Dean. Five shots each, that was the bet. He said he could take five shots of whiskey before I could finish my five of rum. Dean already knew how stubborn I could be, and the prize was even more motivation. If I won, he'd let me drive the Impala for a whole week, wherever we went. And if I lost, I had to make the grocery runs for us for a month straight.

I slammed my shot glass down on the counter seconds before Dean did the same. By now, I was thoroughly sauced. Actually, way more than 'sauced'. I was practically shit-faced. My words came out as one long run-on sentence as I cheered my victory.

"Suck it Dean Winchester!" I said in a rush, my seat wobbling.

"Whoa, slow down there. Little early for celebration there Miss Captain Morgan," Dean chuckled, putting a foot on the lower rung of my stool to keep me from toppling.

"Early? I totally won that bet!"

"Oh no you didn't Gracie," Dean said, smirking at me. "I did. You'd better get used to buying pie. Lots and lots of pie."

I gave him an incredulous look. He just sat there, smug in his lie of a victory. There was no way! I had won that bet, fair and square. And there was no way anybody was going to take away my rightfully earned Impala driving privileges. I could feel the eyes of the bartender watching us, waiting to see what would happen next.

I turned to him. "Have you been watching us this whole time?" He looked between Dean and I before answering.

"Yeah, I suppose I have."

"Then who finished first?"

He held up both hands, palms facing out. "I'm not getting in the middle of this-"

"Who won?" I prompted again, leaning forward to look at him.

He heaved a sigh. "You did little lady. No doubt."

"Ha! I knew it!" I pointed at Dean, falling forward onto the bar in my haste. "I am driving that car!"

Dean shook his head, failing to suppress a grin. He took one last swig from his beer before handing the bartender a few bills and standing up. "Yeah, okay. But not tonight. Let's get you home, eh Calamity Jane?"

He came to my right, hand sliding expertly across my back and over to my waist. As I slid off the bar-stool I could feel his fingers press into my side, trying to hold me up. That friendly pressure on my skin caused a flutter to erupt in my stomach. He then grabbed the hand of mine closest to his side and slung it over his shoulder.

I was vaguely aware of Dean guiding me out of the bar, I was too enveloped in the fact that I had won the bet. I had won a bet against Dean freaking Winchester! And I was going to be able to drive his Baby, that beautiful car I had always dreamed of driving. And for a whole week!

"Gracie? Gracie, you in there?" Dean asked, snapping his fingers in front of my face as we made our way down the sidewalk.

I shook my head. "Nope. I'm in your car."

Dean just laughed at me. It was a warm sound, something I hadn't heard in what felt like forever. The sound of it washed through me, making me feel warm again just as I had when we'd cracked open those first two beers. As we walked, I felt Dean's arm around me and mine slung over his shoulders. Maybe it was the alcohol, but everywhere we made contact felt warm, almost electrically charged.

I focused on this as we entered the motel parking lot, heading to the room at the corner. We stopped at the door and Dean let go of my hand over his shoulder, digging his own into the pocket of his jeans. As soon as he produced the key I felt my eyes begin to droop.

"Whoa there," Dean murmured close to my ear, catching me before I slid off of him and onto the carpet of the motel room as we entered. His breath tickled my ear and I smiled, holding in a giggle. I may have been drunk, but I wasn't _that_ drunk.

Dean swung my arm off of him and slid his other under the backside of my legs. In one fluid motion he was holding me there, and carrying me over to the bed. I couldn't help but let my mind wander into fantasy-land.

Apparently in my wandering, Dean's name had slipped out of my mouth rather loudly.

"Shhh, Gracie, Sam's asleep," Dean hissed to me. His head turned to look at Sam in the other bed, sprawled out, limbs hanging off the side. As Dean reached the second bed I let my arms fall from his neck and, letting gravity pull me down, caused both of us to fall onto the bed.

I could feel Dean's body hover over mine and I laid a hand on his cheek, his stubble scratching my palm lightly. His eyes darted down to me and I looked back at him. We stayed like that for a good thirty seconds.

And in that small amount of time, I came to a decision. Dean had been forced to sleep on the small loveseat sofa for the past three nights of this hunt. We just couldn't afford two rooms this time, hustling pool wasn't paying off as much as it usually did. And even though he acted okay with it, I knew it was really screwing with what little sleep he did get. He would always be up before Sam and I, eyes bloodshot and he usually had a hand rubbing the back of his neck. I didn't want him to have to deal with all that _and _a hangover in the morning. He'd been drinking a considerable amount more than I had.

"Sleep with me," I blurted out quietly. Poor choice of words for what I was actually suggesting, I'll admit. But I'm blaming the alcohol for that one.

"Grace, I-" Dean began, unsure what to do. The hand I had resting on his waist began to fall off as he pulled back, trying to avert and awkward situation by just standing up. I pushed him back down on top of me, his elbow landing next to me on the pillow under my head. His eyes roamed back across me and stopped at my lips briefly before flicking back to my eyes.

"I mean... sleep with me," I said, slightly jerking my head to Sam on the other bed, drooling on his pillow a bit. Dean looked back at Sam and then at me again.

"I've got the..." he began. What I did next was definitely the alcohol.

My arms wrapped around his neck and I pulled down as hard as I could. "No," I said simply as he fell onto the bed, his leg on top of mine. I felt that familiar rush I always did when I inhaled the scent that came off of him: whiskey, leather, and a kind of Dean-scent I couldn't identify.

"Okay, _okay_ Gracie. Jesus," he chuckled. I let my arms relax and Dean buried his face in the pillow next to me, letting himself realize how tired he actually was. I sat up, trying to force my shoes off. As I removed my pants and changed my shirt I fell back on the bed next to him. He was still lying as I had left him, but as I looked over I realized he'd removed his shirt. I laughed and crawled down the bed toward his feet. Just as I thought, he still had his shoes on.

"Gracie, what're you doing?" Dean moaned into the pillow, his voice muffled and tired. I didn't bother to answer as I pulled the first shoe off. I could hear him quietly laughing into his pillow as I tossed both shoes onto the floor. Once I had crawled back up next to him he turned to look at me.

"You sure are a flirty drunk," he smiled.

"Don't act like you don't like it." I tangled myself and Dean under the covers and snuggled up next to him, one hand snaking around his arm and the other across his back. I could feel him next to me, tensing up briefly at my intimacy, but much to my surprise he relaxed into me. Still feeling the over-confidence of the booze in my system I pulled my face close to his and planted a slow kiss on his cheekbone.

"G'night Dean," I breathed before closing my eyes and resting my head on the pillow. I heard his breathing relax after I became still and I listened to it, half-retreating into my thoughts.

Maybe my feelings weren't as one-sided as I had believed. I smiled at the idea and shuffled a bit closer to him. Perhaps out of exhaustion or comfort, I didn't know, Dean pulled his arm from my grip and draped it over my shoulders, inviting me closer. I smiled wider and placed my now free hand on the side of his neck, tucking my ear to his chest.

I fell asleep, listening to him breathe easy.


	2. Chapter 2

Morning came, and with it so did the hangover. At first when I opened my eyes, I didn't recall what had happened much last night after I'd won the bet. But lying in bed, still tangled in Dean's arms I smiled to myself. I breathed in deeply, taking his aroma and warmth into my lungs. He just smelled so good, there was nobody else that smelled like he did. It was just... _Dean_. I let out a slow breath, happy and content despite the headache I knew would be hitting me soon. For a good few minutes I just laid there, listening to him breathe.

He was still asleep. That fact made me very happy. I inched my head far enough away from his chest without waking him to look up at his face. For the first time since I'd met the Winchesters, it looked peaceful. He looked so content and calm, I didn't want to move any further for fear of waking him. So I just snuggled as gently as I could back to his chest and pressed my ear down, his heartbeat filling my ears. It was a nice sound; strong, steady and calm. My eyes closed again and I could feel the sun begin to peek in through the motel room's curtains, sprinkling itself over the bed. I relished in the silence before I heard a noise that nearly caused me to jump.

It was Sam's voice, low and deep so as not to wake us. "Fucking finally, Jesus," he said, a low laugh escaping him. I felt my heart flutter in my chest at his words. Was it really that obvious that I had a crush on Dean? I almost laughed at myself. 'A crush' was not enough to describe my feelings, and 'huge crush' didn't quite cut it either.

I listened to Sam in the tiny half-kitchen across the room making coffee, trying to just make this moment last as long as I could. I didn't know how Dean would react when he woke up and realized we'd slept in the same bed last night. More than half of me hoped he'd be as okay with it as he was last night, but that last little fourth of my brain knew he'd been smashed when he'd agreed to sleeping in the bed. I clenched my jaw, still keeping my eyes shut. Fear twanged across my stomach as I thought of the many ways this day could play out once Dean woke.

Caught up in my thoughts, I jumped a little at the sound of Sam's chair scraping across the tile as he stood up. His footsteps were loud and then quiet as he crossed to the carpet, nearing our bed. I laughed to myself in my head. _Our _bed. The phrase was so strange flitting across my thoughts like that, but it felt nice. I was so caught up thinking about that I was startled at Sam's knuckles nudging my shoulder.

"Grace," he whispered, nudging me again. I slowly let my eyes open, trying not to let on that I'd been awake for the last ten minutes. As I carefully disentangled my limbs from Dean Sam held a cup of coffee out to me. Grateful I took it and sipped before looking up at him.

The look on Sam's face was just one of smug satisfaction. It confused me as I watched him stare down at me, taking another swallow of coffee. "What?" I asked, curious.

"What? Really?" he laughed softly. "You, Gracie. And my brother. I see you guys got a little..." he let the sentence trail off into nothing, cocking an eyebrow to finish it. I could feel my heart speed up in my chest and I gripped my coffee mug tighter in my hands.

"Oh, Sam, no I-"

"It's fine Gracie. I think I knew it was gonna happen before you did."

I shook my head, laughing. I smiled at him. "You dirty-minded little shit." I grinned. "We didn't _sleep_ together. We just... slept together."

Now it was Sam's turn to laugh as he shifted, standing next to the bed. "Right, sure. You expect me to believe that?"

My mouth opened in semi-shock. I knew he wouldn't believe me as the words left my lips, but I had hoped. "It's the truth Sam. We were both seriously drunk last night. And if you had stayed, you would've seen how tired we were. I just figured he should sleep in a bed before we had to hit the road today." I took another gulp of coffee, relaxing as I felt the warmth tickle my throat. "And by the way, we had a bet. I'm driving to the next job."

Sam's eyebrows raised. "Wow," was all he said. He finished his coffee and crossed back to the kitchen, setting the mug in the sink. I sat on the bed, shaking my head and taking in more coffee. Anything I could do to put off the inevitable hangover. My skin erupted in goose bumps when I felt a warm hand trail up my shirt and onto my back, searching for what I didn't know.

I turned and saw Dean rubbing one eye with the palm of his hand. He let his other hand linger on my lower back as he opened both eyes. Sam walked back over now and looked down at him from the end of the bed.

"Have a good time last night Dean?" he chuckled, glancing at me before looking back at his brother for a response.

"Shuddup Sammy," Dean mumbled, still groggy. Clearly his hangover was hitting a bit faster than mine.

"I'm gonna go grab some breakfast," Sam said, still grinning at both of us, holding in a chuckle. I gave him a mock-glare as he crossed to the table and grabbed the Impala's keys, slipping quietly out the door.

I watched the door latch shut before turning my head to look at Dean again. He'd let his hand flop over the side of the bed, eyes still closed. I expected him to say something, but he was quiet for at least two minutes before I broke the silence.

"Dean?"

His face twitched, startled by my voice. He opened his eyes and turned his head to look at me, a small smile playing across his lips as he replied, "Yeah?"

I silently held my coffee mug out to him and he smiled fully, sitting up. He took it from me, his rough, calloused fingers brushing the back of my smooth hand. The small exchange caused my stomach to flutter, questions just burning at the back of my throat. But I held them in, wanting to savor the moment. God knows as soon as I open my mouth I'd mar it with an awkward question or expression.

Dean took a large swig from my mug before leaning back and setting it on the bed-side table. He looked briefly at me before hanging his head to stare at a stray thread in the bed sheet he was fiddling with between his fingers. His other hand was propping him up from behind, his fingers just inches away from where I was sitting.

I really couldn't think of anything to say. The look on his face made my heart ache just a little. It was one of guilt and regret. I couldn't help but wonder why. We hadn't _done_ anything, he had nothing to feel guilty about. Sure, we'd both been really drunk last night and gotten kind of cuddly, but that was nothing to feel guilty about. It wouldn't have happened if the feelings weren't already there.

My stomach twisted as I came to a realization. Maybe he looked guilty because he'd led me on. I didn't blame him, I was always a flirty drunk. But he knew that, I'd gotten drunk with him and Sam on multiple occasions, and it had never seemed to bother either of them. I bit my lip, staring at the side of his face, wondering what to do. I couldn't for the life of me think of anything to say. I looked at him for a few more seconds before I gingerly laid my hand on top of his.

At my touch he looked up and his expression softened. That devious, Dean Winchester half-smile played up at the corner of his mouth and I couldn't help but smile back. "You okay?" I murmured, afraid of my own voice being too loud. It didn't really matter, but I wanted any advance I made to be gentle. Sam had filled me in on more than one occasion about Dean's history with women. Now, after talking to him this morning, I realized he'd been trying to give me advice. About getting with Dean. His brother. Oh Sam, you cheeky little shit you.

Dean nodded in response, looking back down at his lap. His fingers tickled my palm behind us and I rubbed the side of his hand with my thumb. I was just looking at him, letting the silence eat away at us. It was driving me nuts. I wanted to know so many things. Had it just been the alcohol? Did he just need someone for the night because he had been feeling low? What did this mean for our friendship? Was it going to be awkward? Or did he really like me back? The thought made me laugh in my head. This was Dean Winchester we were talking about, there was no way he'd have feelings for me. I knew his type, and I wasn't it.

More than anything I wanted to tell him how I felt. That I wasn't mad if the answer was 'we were just drunk, it didn't mean anything'. I was grateful it had even happened in the first place. I wasn't going to make him feel bad if he didn't like me, that was the shittiest feeling in the world, and I knew it better than most. I could feel the words pooling right under my chin like a scream, and in a rush I just blurted them out.

"Dean, it's okay. I know we were both seriously shit-faced last night. You know I get flirty when I'm drunk, and I know how you are too. I just felt... I don't know. I just wanted you to get one good night's sleep for once is all," I said. Part of that was a lie. I knew how I felt, but without the confidence of alcohol I had no resolve to tell him.

He looked at me, his brow furrowing in frustration and confusion. I blinked at him, swallowing my nervousness. I was at a loss for what else to do if he didn't say anything. Luckily for me, he did.

"Gracie I... I know it's okay. I'm sorry, I'm not good at all this touchy-feely crap." He laughed a little, averting his gaze from my face and back down to the bed sheets for a moment. "I just don't... I don't want that to be a one time thing."

I opened my mouth to respond with 'I know Dean, one time thing. We were drunk.' but the words didn't come out. His response had almost literally knocked the wind out of me. Now it was my turn to look at him with my eyebrows knitted together like a caterpillar. What the hell was going on? Was I _dreaming?_

He laughed at my gaping face, eyes darting down to my mouth before going back up again. "You idiot," he breathed, reaching for the coffee again. He drained the mug and laid back down, digging both hands into his eyes. The lack of warmth on my palm now made me feel a sense of longing in my chest. I focused on that feeling, a bit of pent up excitement mingling with it. I built it up with my lungs, taking a deep breath. If he was going to call me an idiot, I was going to act like one.

With one more deep, not-so-calming breath I moved from my sitting position. As gracefully as I could I swung a leg over him, resting myself just above his hips. Now sitting on him I put both hands on his chest and just felt his stomach rise and fall with his breath. I stared down at his chest, my eyes snaking up to the sun-burst anti-possession tattoo nestled just below his left collarbone. I could feel his eyes on me now, causing my face to flush. I knew I was as red as a tomato right now, but I just kept staring.

His hands on my forearms startled me. My eyes darted to his and he stared back at me, my own curiosity and longing reflected back in his gaze. I could feel my heart pumping wildly as he traced his fingers up and down the side of my arms. I think he could tell how nervous I was, but it seemed not to bother him.

Resolving to do what I had set out to in the first place I pressed my lips into a hard line and with one breath, ran my hands up his chest and back around to lock together behind his neck. Our faces were so close now I could feel his breath tickle my eyelashes. His hands were at my sides, gently holding my waist. Dean's fingers were still on the fabric of my shirt, which I now realized was actually his. In the dark last night I had grabbed a shirt off the bed, and it happened to be the one he'd discarded while I wasn't looking. I smiled slightly and he squeezed my sides reassuringly, letting out a breath. I hadn't realized, but he'd been holding it in as soon as I'd moved closer to him.

The tension now was mounting, and I we could both feel it. I knew I was too nervous now, the back of my neck tingling with an excited prickle. My throat felt constricted, almost sick. With another wave of fear I remembered my hangover. Please for the love of God do not let me get sick now.

Without warning, Dean tilted his head to the side and rose, taking me with him. His lips pressed into mine with a gentle pressure as his arms wrapped around me fully now, hugging my body to his chest so I wouldn't fall back. My eyes slid closed and I kissed back, my arms tightening around his neck. My brain was a frenzied mess as I focused on the feel of his lips on mine. He was so surprisingly tender with me, his kiss hovering and sweet on my mouth as though if he kissed me too hard I'd break.

All those weeks of pining for him pushed me forward, closer to his face with mine. I kissed him harder, not wanting to break away. How was this happening? We weren't drunk, _how_ was this _happening_? His arms moved now, one staying on my back pressing me to him and the other going up to my face. Dean's thumb brushed my cheekbone, the tips of his fingers mussing my short hair. He gently dug his short fingernails into the skin of my neck and more goose bumps erupted down my spine.

I rubbed my hands on his shoulders as we pulled back simultaneously. I opened my eyes and found him looking at me, a happy glint in his emerald eyes. I studied them, noting how closer to the inside a ring of hazel surrounded his pupil, nearly matching the color of aged whiskey. My smile couldn't be contained and I grinned at him idiotically.

His lips parted to speak but I moved my hands to his face. My fingers brushed over his stubble and I smiled again, laughing a little bit. I wouldn't have been surprised if I was glowing. I hadn't felt this happy in such a long time, I just wanted this moment to linger. The sun illuminated Dean's face and I felt its warmth on the side of mine as well, its heat mirroring the feeling in my stomach now. It was one of disbelief and great joy. I focused on it as I hugged him, kissing his cheek as I went.

The force of my hug took him by surprise and before either of us could stop it we fell back on the bed, my giggling uncontainable now. I could hear him laughing under me, our stomachs pressing together. The sound of his happiness made my heart flutter again in time with my stomach. And the knowledge that I had done this for him made me smile wider into the pillow my face had landed in. His hands wrapped around my back again and lightly scratched it. We stayed like that for a minute or so before he spoke.

"We should probably get dressed," he muttered in my ear, his voice gruff and low. The sound of it so close to me gave me goose bumps for a moment.

"Yeah probably. If Sam found us like this he'd never let it go," I agreed, sitting up on top of him again.

Dean smiled up at me and I looked back. At least now I knew we'd both keep flirting with each other, drunk or not.


End file.
